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Total Synthesis of Sekothrixide Strategically Utilizing Regioselective Coupling of TMS-Protected Epoxy sec-Alcohol with Gilman Reagent

Author:
Katsumi, Daisuke, Nakasone, Kazuki, Terayama, Naoki, Yasui, Eiko, Mizukami, Megumi, Miyashita, Masaaki, Nagumo, Shinji
Source:
Journal of organic chemistry 2019 v.84 no.3 pp. 1553-1562
ISSN:
1520-6904
Subject:
chemical reactions, chemical structure, epoxides, organic chemistry, regioselectivity
Abstract:
A new efficient synthesis of sekothrixide was established on the basis of our developed regioselective coupling of epoxy sec-alcohol with Gilman reagent guided by a TMS group. The new synthetic route allowed an overall yield of 6.3% (26 steps) from optically active 3-silyloxy-2-methylaldehyde.
Agid:
6296583